[bis((1S)-1-(benzyloxymethyl)allyloxy)phosphoryl]acetic acid ethyl ester | 566915-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [bis((1S)-1-(benzyloxymethyl)allyloxy)phosphoryl]acetic acid ethyl ester
• 英文别名: ethyl 2-bis[[(2S)-1-phenylmethoxybut-3-en-2-yl]oxy]phosphorylacetate
• CAS: 566915-05-7
• 化学式: C₂₆H₃₃O₇P
• 分子量: 488.518
• InChiKey: MWDSULYBNGGKPW-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [bis((1S)-1-(benzyloxymethyl)allyloxy)phosphoryl]acetic acid ethyl ester 在 dirhodium tetraacetate 、 对甲苯磺酰叠氮 、 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (1R,2R,4S,5R)-4-Benzyloxymethyl-2-((S)-1-benzyloxymethyl-allyloxy)-2-oxo-3-oxa-2λ⁵-phospha-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Substituent effects in the double diastereotopic differentiation of α-diazophosphonates via intramolecular cyclopropanation

  摘要：

  The investigation of substituent effects in the double diastereotopic differentiation of substituted alpha-diazophosphonates using intramolecular cyclopropanation catalyzed by Rh-2(OAc)(4) is reported. Carbene facial selectivity in these transformations is dictated by substrate control in either of two ways: (i) exploitation of (R)-pantolactone as an auxiliary incorporated into the carboester functionality while probing olefinic substituent effects, or (ii) utilization of chiral, non-racemic allylic alcohols incorporated into the phosphonate moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00081-8
• 作为产物：
  描述：

  ethyl dichlorophosphonoacetate 、 (S)-1-(benzyloxy)but-3-en-2-ol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以100 mg的产率得到[bis((1S)-1-(benzyloxymethyl)allyloxy)phosphoryl]acetic acid ethyl ester
  参考文献：
  名称：

  Substituent effects in the double diastereotopic differentiation of α-diazophosphonates via intramolecular cyclopropanation

  摘要：

  The investigation of substituent effects in the double diastereotopic differentiation of substituted alpha-diazophosphonates using intramolecular cyclopropanation catalyzed by Rh-2(OAc)(4) is reported. Carbene facial selectivity in these transformations is dictated by substrate control in either of two ways: (i) exploitation of (R)-pantolactone as an auxiliary incorporated into the carboester functionality while probing olefinic substituent effects, or (ii) utilization of chiral, non-racemic allylic alcohols incorporated into the phosphonate moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00081-8

文献信息

• Substituent effects in the double diastereotopic differentiation of α-diazophosphonates via intramolecular cyclopropanation
  作者：Joel D. Moore、Paul R. Hanson

  DOI：10.1016/s0957-4166(03)00081-8

  日期：2003.4

  The investigation of substituent effects in the double diastereotopic differentiation of substituted alpha-diazophosphonates using intramolecular cyclopropanation catalyzed by Rh-2(OAc)(4) is reported. Carbene facial selectivity in these transformations is dictated by substrate control in either of two ways: (i) exploitation of (R)-pantolactone as an auxiliary incorporated into the carboester functionality while probing olefinic substituent effects, or (ii) utilization of chiral, non-racemic allylic alcohols incorporated into the phosphonate moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.